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Horsetail plant (Equisetum arvense) and horsetail plant ash: application and comparison of their catalytic activities as novel and natural porous lewis acid catalysts for the one-pot green synthesis of 2-amino-4H-chromene derivatives under solvent-free conditions

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Abstract

This study aims to use a new medicinal porous plant having a high content of silica known as horsetail and horsetail ash for the first time as novel, efficient, and environmentally friendly natural mild catalysts. The structure of these catalysts was characterized by different techniques such as FT-IR, XRF, SEM–EDS, N2 adsorption–desorption, XRD, and ICP analysis. The results obtained from the analysis revealed that both horsetail and horsetail ash could act as a solid acid catalyst. In addition, a further detailed analysis illustrated that they have a different surface area, porosity, and crystalline structure which can affect their catalytic activities. The synthesis of 2-amino-4H-chromene derivatives was performed via a one-pot three-component condensation of dimedone, malononitrile, and various aromatic aldehydes to compare their catalytic activities under solvent-free conditions. Due to its high porosity and high surface area, horsetail ash yields better results compared to the horsetail itself. FT-IR, mass, 1H-NMR, and 13C-NMR spectroscopies were used to identify the synthesized compounds in this study. An important advantage of this method is the use of these effective natural catalytic systems with characteristics such as low cost, mild reaction conditions, nontoxicity, and reusability which resulted in corresponding products in high to excellent yields and proper reaction times.

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References

  1. R.C. Cioc, E. Ruijter, R.V.A. Orru, Green Chem. 16, 2958 (2014)

    Article  CAS  Google Scholar 

  2. T.J.J. MŘller, R.V.A. Orru, V.A. Chebanov, Y.I. Sakhno, V.E. Saraev, E.A. Muravyova, A.Y. Andrushchenko, S.M. Desenko, V.R. Akhmetova, G.R. Khabibullina, Multi-component Reactions In Heterocyclic Chemistry (Springer, New York, 2011), pp. 31–73

    Google Scholar 

  3. K. Görlitzer, A. Dehne, E. Engler, Arch. Pharm. 316, 264 (1983)

    Article  Google Scholar 

  4. S.J. Mohr, M.A. Chirigos, F.S. Fuhrman, J.W. Pryor, Cancer Res. 35, 3750 (1975)

    CAS  PubMed  Google Scholar 

  5. T. Raj, R.K. Bhatia, R.K. Sharma, V. Gupta, D. Sharma, M.P.S. Ishar, Eur. J. Med. Chem. 44, 3209 (2009)

    Article  CAS  PubMed  Google Scholar 

  6. P. Vats, V. Hadjimitova, K. Yoncheva, A. Kathuria, A. Sharma, K. Chand, A.J. Duraisamy, A.K. Sharma, A.K. Sharma, L. Saso, S.K. Sharma, Med. Chem. Res. 23, 4907 (2014)

    Article  CAS  Google Scholar 

  7. M.K. Manion, D. Hockenbery, Cancer Biol. Ther. 2, 104 (2003)

    Article  Google Scholar 

  8. Z.Q. Xu, K. Pupek, W.J. Suling, L. Enache, M.T. Flavin, Bioorg. Med. Chem. 14, 4610 (2006)

    Article  CAS  PubMed  Google Scholar 

  9. E. Mosaddegh, A. Hassankhani, G. Mansouri, E.-J. Chem. 8, 529 (2011)

    Article  CAS  Google Scholar 

  10. A. Khazaei, F. Gholami, V. Khakyzadeh, A.R. Moosavi-Zare, J. Afsar, RSC Adv. 5, 14305 (2015)

    Article  CAS  Google Scholar 

  11. Y. Ren, W. Zhang, J. Lu, K. Gao, X. Liao, X. Chen, RSC Adv. 5, 79405 (2015)

    Article  CAS  Google Scholar 

  12. H.R. Safaei, M. Shekouhy, S. Rahmanpur, A. Shirinfeshan, Green Chem. 14, 1696 (2012)

    Article  CAS  Google Scholar 

  13. M.R. Islami, E. Mosaddegh, Phosphorus Sulfur 184, 3134 (2009)

    Article  CAS  Google Scholar 

  14. X.-S. Wang, D.-Q. Shi, S.-J. Tu, C.-S. Yao, Synth. Commun. 33, 119 (2003)

    Article  CAS  Google Scholar 

  15. S. Balalaie, M. Sheikh-Ahmadi, M. Bararjanian, Catal. Commun. 8, 1724 (2007)

    Article  CAS  Google Scholar 

  16. S.-J. Tu, Y. Gao, C. Guo, D. Shi, Z. Lu, Synth. Commun. 32, 2137 (2002)

    Article  CAS  Google Scholar 

  17. I. Devi, P.J. Bhuyan, Tetrahedron Lett. 45, 8625 (2004)

    Article  CAS  Google Scholar 

  18. S. Tu, H. Jiang, Q. Zhuang, C. Miao, D. Shi, X. Wang, Y. Gao, Chin. J. Org. Chem. 23, 488 (2003)

    CAS  Google Scholar 

  19. O.H. Qareaghaj, S. Mashkouri, M.R. Naimi-Jamal, G. Kaupp, RSC Adv. 4, 48191 (2014)

    Article  CAS  Google Scholar 

  20. L. Sapei, Characterisation of silica in Equisetum hyemale and its transformation into biomorphous ceramics, pp. 1–158 (2007)

  21. G. Holzhüter, K. Narayanan, T. Gerber, Anal. Bioanal. Chem. 376, 512 (2003)

    Article  PubMed  CAS  Google Scholar 

  22. D. Cloutier, A.K. Watson, Weed Sci. 33, 358 (1985)

    Article  Google Scholar 

  23. F.H.M. Do Monte, J.G. dos Santos, M. Russi, V.M.N.B. Lanziotti, L.K.A.M. Leal, G.M. de Andrade Cunha, Pharmacol. Res. 49, 239 (2004)

    Article  PubMed  Google Scholar 

  24. H. Oh, D.H. Kim, J.H. Cho, Y.C. Kim, J. Ethnopharmacol. 95, 421 (2004)

    Article  CAS  PubMed  Google Scholar 

  25. H. Mekhfi, M. El Haouari, A. Legssyer, M. Bnouham, M. Aziz, F. Atmani, A. Remmal, A. Ziyyat, J. Ethnopharmacol. 94, 317 (2004)

    Article  PubMed  Google Scholar 

  26. N.S. Sandhu, S. Kaur, D. Chopra, Asian J. Pharm. Clin. Res. 3, 146 (2010)

    CAS  Google Scholar 

  27. S. Soleimani, F.F. Azarbaizani, V. Nejati, Pak. J. Biol. Sci. 10, 4236 (2007)

    Article  PubMed  Google Scholar 

  28. N. Radulović, G. Stojanović, R. Palić, Phytother. Res. 20, 85 (2006)

    Article  PubMed  CAS  Google Scholar 

  29. M. Veit, C. Weidner, D. Strack, V. Wray, L. Witte, F.C. Czygan, Phytochemistry 31, 3483 (1992)

    Article  CAS  Google Scholar 

  30. A. Carnet, C. Petitjean-Freytet, D. Muller, J. Lamaison, Plants Med. Phytother. 25, 32 (1991)

    Google Scholar 

  31. J.G. dos Santos Junior, F.H.M. do Monte, M.M. Blanco, VMdNB Lanziotti, F.D. Maia, L.K. de Almeida Leal, Pharmacol. Biochem. Behav. 81, 593 (2005)

    Article  CAS  Google Scholar 

  32. M. Veit, K. Bauer, H. Geiger, F.C. Czygan, Planta Med. 58, 697 (1992)

    Article  Google Scholar 

  33. B. Fabre, B. Geay, P. Beaufils, Plantes Med. Phytother. 26, 190 (1993)

    CAS  Google Scholar 

  34. C. Beckert, C. Horn, J.P. Schnitzler, A. Lehning, W. Heller, M. Veit, Phytochemistry 44, 275 (1997)

    Article  CAS  Google Scholar 

  35. T. Řezanka, Phytochemistry 47, 1539 (1998)

    Article  Google Scholar 

  36. F. Adam, K. Kandasamy, S. Balakrishnan, J. Colloid Interface Sci. 304, 137 (2006)

    Article  CAS  PubMed  Google Scholar 

  37. B.M. Cherian, L.A. Pothan, T. Nguyen-Chung, G. Mennig, M. Kottaisamy, S. Thomas, J. Agric. Food Chem. 56, 5617 (2008)

    Article  CAS  PubMed  Google Scholar 

  38. X. Sun, F. Xu, R. Sun, P. Fowler, M. Baird, Carbohydr. Res. 340, 97 (2005)

    Article  CAS  PubMed  Google Scholar 

  39. D. An, Y. Guo, Y. Zhu, Z. Wang, Chem. Eng. J. 162, 509 (2010)

    Article  CAS  Google Scholar 

  40. L. Sapei, N. Gierlinger, J. Hartmann, R. Nöske, P. Strauch, O. Paris, Anal. Bioanal. Chem. 389, 1249 (2007)

    Article  CAS  PubMed  Google Scholar 

  41. P. Yuan, P.D. Southon, Z. Liu, M.E.R. Green, J.M. Hook, S.J. Antill, C.J. Kepert, J. Phys. Chem. C 112, 15742 (2008)

    Article  CAS  Google Scholar 

  42. M. Thommes, Chem. Ing. Tech. 82, 1059 (2010)

    Article  CAS  Google Scholar 

  43. N. Yalcin, V. Sevinc, Ceram. Int. 27, 219 (2001)

    Article  CAS  Google Scholar 

  44. M.G. Dekamin, M. Eslami, Green Chem. 16, 4914 (2014)

    Article  CAS  Google Scholar 

  45. M.A. Zolfigol, N. Bahrami-Nejad, F. Afsharnadery, S. Baghery, J. Mol. Liq. 221, 851 (2016)

    Article  CAS  Google Scholar 

  46. A. Rostami, B. Atashkar, H. Gholami, Catal. Commun. 37, 69 (2013)

    Article  CAS  Google Scholar 

  47. S. Rostamnia, A. Nuri, H. Xin, A. Pourjavadi, S.H. Hosseini, Tetrahedron Lett. 54, 3344 (2013)

    Article  CAS  Google Scholar 

  48. S. Balalaie, M. Bararjanian, M. Sheikh-Ahmadi, S. Hekmat, P. Salehi, Synth. Commun. 37, 1097 (2007)

    Article  CAS  Google Scholar 

  49. R.-Y. Guo, Z.-M. An, L.-P. Mo, R.-Z. Wang, H.-X. Liu, S.-X. Wang, Z.-H. Zhang, ACS Comb. Sci. 15, 557 (2013)

    Article  CAS  PubMed  Google Scholar 

  50. M.A. Zolfigol, M. Safaiee, N. Bahrami-Nejad, New J. Chem. 40, 5071 (2016)

    Article  CAS  Google Scholar 

  51. M. Amirnejad, M.R. Naimi-Jamal, H. Tourani, H. Ghafuri, Monatsh. Chem. 144, 1219 (2013)

    Article  CAS  Google Scholar 

  52. S. Gao, C.H. Tsai, C. Tseng, C.-F. Yao, Tetrahedron 64, 9143 (2008)

    Article  CAS  Google Scholar 

  53. P. Sharma, M. Gupta, R. Kant, V.K. Gupta, RSC Adv. 6, 32052 (2016)

    Article  CAS  Google Scholar 

  54. B. Sadeghi, A. Hassanabadi, S. Bidaki, J. Chem. Res. 35, 666 (2011)

    Article  CAS  Google Scholar 

  55. H. Naeimi, M. Farahnak Zarabi, Appl. Organomet. Chem. 32, e4225 (2018)

    Article  CAS  Google Scholar 

  56. S. Nemouchi, R. Boulcina, B. Carboni, A. Debache, C. R. Chim. 15, 394 (2012)

    Article  CAS  Google Scholar 

  57. S. Banerjee, A. Horn, H. Khatri, G. Sereda, Tetrahedron Lett. 52, 1878 (2011)

    Article  CAS  Google Scholar 

  58. V. Safarifard, S. Beheshti, A. Morsali, CrystEngCommun 17, 1680 (2015)

    Article  CAS  Google Scholar 

  59. S. Pradhan, V. Sahu, B.G. Mishra, J. Mol. Catal. A Chem. 425, 297 (2016)

    Article  CAS  Google Scholar 

  60. A. Maleki, R. Ghalavand, R. Firouzi Haji, Appl. Organomet. Chem. 32, e3916 (2018)

    Article  CAS  Google Scholar 

  61. Y. Sarrafi, E. Mehrasbi, A. Vahid, M. Tajbakhsh, Chin. J. Catal. 33, 1486 (2012)

    Article  CAS  Google Scholar 

  62. K. Niknam, M. Khataminejad, F. Zeyaei, Tetrahedron Lett. 57, 361 (2016)

    Article  CAS  Google Scholar 

  63. A. Hasaninejad, M. Shekouhy, N. Golzar, A. Zare, M.M. Doroodmand, Appl. Catal. A Gen. 402, 11 (2011)

    Article  CAS  Google Scholar 

  64. M. Abdollahi-Alibeik, F. Nezampour, React. Kinet. Mech. Catal. 108, 213 (2013)

    Article  CAS  Google Scholar 

  65. R.S. Bhosale, C.V. Magar, K.S. Solanke, S.B. Mane, S.S. Choudhary, R.P. Pawar, Synth. Commun. 37, 4353 (2007)

    Article  CAS  Google Scholar 

  66. B. Maleki, S.S. Ashrafi, RSC Adv. 4, 42873 (2014)

    Article  CAS  Google Scholar 

  67. D. Azarifar, S.M. Khatami, M.A. Zolfigol, R. Nejat-Yami, J. Iran. Chem. Soc. 11, 1223 (2014)

    Article  CAS  Google Scholar 

  68. R. Heydari, R. Rahimi, M. Kangani, A. Yazdani-Elah-Abadi, M. Lashkari, Acta Chem. Iasi 25, 163 (2017)

    Article  Google Scholar 

  69. A.A. Mohammadi, M.R. Asghariganjeh, A. Hadadzahmatkesh, Arab. J. Chem. 10, S2213 (2017)

    Article  CAS  Google Scholar 

  70. P. Bhattacharyya, K. Pradhan, S. Paul, A.R. Das, Tetrahedron Lett. 53, 4687 (2012)

    Article  CAS  Google Scholar 

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Acknowledgements

We are thankful to Ferdowsi University of Mashhad Research Council for financial support to this work (Grant No: 3/45801).

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  1. Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, 9177948974, Iran

    Nina Hosseini Mohtasham & Mostafa Gholizadeh

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  1. Nina Hosseini Mohtasham
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  2. Mostafa Gholizadeh
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Correspondence to Mostafa Gholizadeh.

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Hosseini Mohtasham, N., Gholizadeh, M. Horsetail plant (Equisetum arvense) and horsetail plant ash: application and comparison of their catalytic activities as novel and natural porous lewis acid catalysts for the one-pot green synthesis of 2-amino-4H-chromene derivatives under solvent-free conditions. J IRAN CHEM SOC 17, 397–409 (2020). https://doi.org/10.1007/s13738-019-01777-1

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